Fear of Flying.

Failure isn’t the worst thing to happen to you in Silicon Valley.

In fact, failure is a rather warm, safe blanket for most folks around these parts. Unlike most places in the world where public failure could ruin your career, destroy a family, or even bring risk of death from shame… in Silicon Valley, everyone is all too comfortable openly discussing their failure(s). While this is generally a good thing — most people won’t learn how to stretch themselves unless they push the boundaries of potential failure — a far greater fear for many entrepreneurs is that of unsustainable success.

Far worse than hitting the ground, most of us are scared shitless of flying high, staying aloft, and keeping arms extended as we climb into a big blue sky, reaching for ever higher heights… Icarus, beware.

Indeed, fear of flying is the most frightening thing ever for truly great entrepreneurs. Usually accompanied by a little voice inside your head saying “Crap. any minute now these fuckers are gonna realize i can’t keep this up very long, and then i won’t be a Golden God anymore.”


Of course it’s easy to fly high for a few days or weeks. Everyone gets lucky, hits their stride with gusto now & then, sinks a sweet 3-pointer once every 20 shots, writes some challenging routine that compiles the 1st time and works flawlessly, or closes a big deal they didn’t think was gonna happen. Sure, you can do that every once in awhile — but can you do it for a month? for a quarter? every day for a year? can you beat last month’s number consistently, and can you say with a straight face you’ll be able to beat that high-water mark again next month too?

Or are you afraid you might come crashing back down to earth? Are you afraid you’ll get tired, and your wings will fail you? Are you afraid you might only be a flightless chicken, with just a really big gust of wind behind you?

Cluck-cluck, motherfucker… we know who’s really behind that Mask of Zorro you’re wearing. Aren’t you scared of flying too?

Cuz I sure as hell am.

To all of us who strive for unlikely outcomes, it is this dual challenge of consistent and regular outperformance which is our real nightmare. In fact, it’s almost certifiably insane to sign up for such a goal — like agreeing to break a world record, and then keep breaking it over and over again, while maintaining perspective and focus, as well as the emotional stability necessary to lead and grow your team. Who the hell believes they can do that? Who the hell isn’t afraid they’ll falter, somewhere along the way?

Yet, it is exactly this fear of flying which sustains us, perhaps even exhilarates us, motivates us to find the passion, stamina, and renewed energy to stay aloft, to continue climbing higher, up and to the right.

And so: I wish you luck, junior birdmen and women. Your task is not an easy one, and many of you will come crashing back to earth, broken and crying. I cannot help you stay aloft, and i cannot help remove the fear — I can only remind you that you’re not alone.

Fly, little bird… spread your wings, and FLY!

We’re right behind you. Godspeed.


This article originally appeared on 500 Hats.